Small Town Good Times

So here I was, living in a small country town. I'd moved in with my Aunt Lydia when my parents divorced a few years back. I was 22 years of age, doing odd jobs around the town. I was content with earning some cash and getting some work experience as well. My Aunt Lydia who was a divorcee worked as a secretary at the local council. We got along just fine, so much that I would say, we had become good friends. I contribute to the running of the house, although Aunt usually does the washing and cooking.

"What on earth are these?" Aunt Lydia said as she stormed through the room holding a pair of my underpants.

"What do you mean?" I asked

"Jason, all your underpants I've washed are either torn or worn. You really need to get a new pair." Aunty said.

"Yeah I know. It's just that I've been busy and haven't had the chance lately" I replied.

"Look, I'll ring Janet, an old friend of mine who makes great clothing designs of all kinds, and she'll fix you some in no time. Save you some money that way" Aunty said.

A week passed, and Aunty Lydia had contacted Janet and gave her my waist measurements. It was only a matter of time before we received a parcel with underwear on our doorstep.

"Here they are, I knew she'd whip them up in no time. She's a clever lady. Try them on and see how they fit" Aunty said holding my new underwear.

"Ok Lydia, I'll try them on in a second" I replied. I watched Aunty as she walked by and noticed her massive breasts. She was a curvy women on top, with a curvy frame. She had just come home from work, and was wearing her grey skirt that finished to her knees, and white buttoned shirt. Her breasts were more then a handful and she allowed about an inch of cleavage by unbuttoning the first few buttons of her top.

As Aunty left the room, I tried on my new jocks. As I tucked my cock into the underwear I felt there was a lack or room at the front. The jocks tended to fit well around the waist, although it was incredibly tight at the front. I wasn't erect or anything, it's just that I was used to my old underwear, which I had grown into. My cock was one of those cocks that would stay four-five inches long when it wasn't erect.

"So I guess you're a big boy" Aunty said from the entrance of my room.

"They're a bit tight at the front" I replied. Aunty walked over to me, and felt the material, casually gliding her hands over my cock.

"Yeah, I think you'll need to see Janet personally, she'll have to custom make you some." Aunty replied. "In the meantime, you can use your old jocks. Or if you like, you can wear nothing, I certainly wouldn't object" Aunty joked as she left the room. I was left with a growing boner.

A week passed and I arranged to meet Janet. I knocked on the door, and we did our introductions. Janet was about in her mid-forties and quite bubbly. She had big curly red hair, and a great set of tits. She was a little more rounder then Aunty Lydia, and maybe her tits were slightly bigger. Both would have easily have been double D's. Janet was wearing tight jeans that really defined her backside, and a tight black T-shirt. What a great pair of tits she had I thought. She had a generous amount of cleavage on display as her top finished rather low. The more she'd bend down, the more view you'd get.

After small talk, we got down to business.

"Now Jason, I'm going have to ask you to remove your clothes so I can get your measurements right" Janet said.

I was kind of nervous, yet excited to get my gear off in front of her. I pulled my shirt off and my slid shorts down. I slid my old jocks off, and Janet picked them up. I stood there naked in front of Janet as she sat on the couch preparing her tape measure.

"Wow, your Aunty did say you were quite a handful, but I didn't know she meant it in that way" Jane commented with a glowing smile on her face. Her eyes focused on my loose 5-inch cock. "I've worked with many men before, and I have to say it's always a pleasure, especially someone like yourself. You've got a lovely penis. I just thought I'd say that, and get it out of the system" Janet said.

"Come here" Janet said. "It's obvious the jocks I sent you were too small around the groin area. I just need to take a measure of your cock, so could you just stand still for a moment". I stood there, as she sat on the couch eye level to my cock. She put her reading glasses on, and began measuring the length of my cock. She seemed very professional and focused. She used the term "cock" in such a way that it seemed like she used the word in every day speech.

Janet put the tape measure against the length of my cock, and noted the length. "Okey, that's 5 inches" she said. Then she'd rap the tape measure around my cock, and then around my testicles, taking note of the size. She looked very professional. As I looked down, I could see a beautiful view of her breasts. She'd press her tits against her knees, and her tits would push out of her top. They were so full.

My cock began to stiffen slightly. Janet noticed that. "It's ok honey, let me just measure it again. Well, so now you're 6 inches", and she scribbled out the previous measurement and wrote the new number. "Now you're not going to keep on growing on me are you" she joked.

"I'll just need to measure your waist again, and see if the measure meant you gave me was correct. Janet stood up, and leaning forward she put the measuring tap around my waist so the end measurement would meet at my rear. She bent forward and around her head went to confirm the number. Meanwhile, my cock pressed against her top, and I could feel the coolness of her cleavage press against it. As she pulled away, my cock had become fully erect.

Janet looked down and smiled at my cock. "What have we here" Janet said. "That's perfectly fine Jason, nothing to be ashamed of. I actually need it in full growth to determine the room the underwear will need to be to accommodate your big cock. Oh gosh you're gorgeous" Janet said as she bent down kissing the head of my cock. "I wish I could have you all to myself." Janet added in a maturely friendly kind of way. I wasn't sure if she was hinting at something or just passing on a complement.

Janet measured my cock again. "Now, that's 8 inches, you're not going to get any larger I hope. Well actually, I wouldn't complain" Janet joked.

"Sorry about this Janet, I just couldn't help myself" I said.

"Oh don't worry honey, it's perfectly normal. Well above average actually" she joked. "Now, I've gotten all the measurements I need, so you can start downsizing, and get dressed".

"Thank's for that, but I don't think this will downsize that easily" I added, as I slid my shorts over my bare cock.

"I'll see you in two days time Jason, it'll give me enough time to tailor a comfortable garage to park that long truck of yours. See if you can hold that till then." Janet joked with a wink.

Two days passed, and I was back at Janet.

"You know the drill sweaty" Janet said. "Get your gear off. I've got two types of underwear for you to try" she said. This time Janet was wearing black loose pants, with a white spaghetti strap singlet top. It was obvious she didn't have a bra on. In fact, her nipples were clearly visible under her singlet. Her singlet held her tits in well though, even if it did provide me plenty of cleavage.

Soon enough I was naked there, as Janet chucked me the first pair of jocks. They were this soft material that seemed to stretch. I pulled them over my cock and they fit just like a glove. "Wow, that feels great" I said.

"I thought so. This material will stretch to accommodate whatever size your cock grows to. It's the same material that my singlet is made of. It helps me hold my boobs in. Let me just feel it" Janet said as she placed her hand on my waist and massaged my groin. I grew hard, and she smiled as she felt my reaction. "See what I mean, you still have enough room to accommodate for those hard moments."

"Now get those off, honey, I want you to put these on. Now, these are exactly the same, except for the G-string at the rear" Janet said. I slipped them on easily as my erection was well contained.

"How's that feel? You look absolutely sexy Jason. Turn around, and bend over. What a great ass you also have. Oh gosh, I'm so excited" Janet yelled.

"You're exited? Spare a thought for me" I said jokingly referring to my cock

"I have to admit Jason. As good as my designs look on you. I would much rather you like this" Janet said as she bent down pulling my underwear to the ground. She held my foot up for me to lift it up and throw the underwear to the side.

Janet stood there smiling at my cock. "You're so hard, and you haven't gotten to these" Janet said as she pulled her singlet top off and let her breasts hang free. "Like em?" Janet asked.

My tongue was half out, as I gawked at her large breasts swaying in front of me.

"There's more of that honey. These slip of as easy as those underpants I designed you" Janet said as she slide her pants down, revealing her bare ass.

Janet cam closer to me. My hands wrapped around her waist as my cock poked her stomach. I could feel her hardened nipples against my chest. I kissed her lips passionately. It felt so good being completely naked and holding her. My head moved down and my hands met her breasts. I massaged her tits in circles with my hands as my mouth came towards her large nipples. She was a big girl alright. I start sucking on her nipples, and licking them in circles. I felt her hands all over me. She began stroking my cock as I sucked, and then started wanking me.

Soon enough, Janet was on her knees, sucking my cock. Her tongue wrapped around it. She'd slide her tongue up and down, and around my balls. Then she'd suck a ball in her mouth, and release it, then move to the next one. Then back up the shaft and to the head of my cock, she would tap my cock against her tongue, and dip it into her mouth. The head would sit her mouth, as her hand wanked my cock. Her other hand would massage my balls. She was a talented lady I tell you.

It was time for me to cum, as she stroked hard. "Cum over my tits" she said, as I moaned and groaned. Before I knew it, I was hosing her breasts with my cum. She stroked every drop onto her breasts, pressing my cock into her breasts.

"Looks like I won't need a shower tonight" Janet said as she rubbed her tits in circles, massaging her soft plump breasts.

"If you want, I can clean your insides too" I added.

She grabbed my half sized cock, and took me to her the couch. She sat on the couch, and stroked my cock, as it hardened to full size again. "Gee that didn't take long" Janet said. Her right hand massaged my cock as her other hand massaged her breasts. "My pussy is really wet, cum and clean my insides honey" Janet said as she lay back on the couch spreading her legs apart.

She had thick legs, to go with her curvy frame. Her skin was smooth. Her tits fell to the left and right as she lay there. I felt her pussy with my finger as I watched her play with her tits. I stroked my cock as I got set to fuck her good. She had a nice shaven pussy, just waiting to be penetrated.

My cock slipped into her vagina as I slowly began pumping her. I held her feet as her legs were split wide apart. I started panting a little as I worked her. Her tits jiggled as I pumped and they slipped out of her hands. I placed a leg over my right shoulder, as my hands started massaging her tits. I pulled at her nipples as she growled and screamed. I wrapped the other leg over my against my chest and her feet crossed around my neck. I rocked her like a boat. Up and down as I saw the pleasure on her face.

Soon enough, I cummed her full. I made sure I polished her insides with cum. As I slowly withdrew my cock, her legs fell to the side. My head rested on her chest, and she stroked the back of my head, as if I had been a good boy. It felt so unreal being wrapped in her arms in all our complete nakedness. She was curvaceous, with her soft skin, huge breast and nice thick ass. I soon realized how much I'd love heavy girls. I would have done her again, but I had to get going.